I have some balloon-head .45 Colt rounds (UMC) loaded with blackpowder. Fired a few, a while back, and they all functioned perfectly - and were faster than modern smokeless rounds. The box is in tatters, with no legible date stamp. I'm guessing 1910s or 20s.
I also have a box of .38 S&W from the 30s. I fired six rounds (in a correctly chambered gun) and all six cases were badly split, so the rest of the box is purely decorative.
I got deeply involved with the .228 Ackley after my grandfather passed his original gun to me in his will. He also included all his notes, correspondence with P.O. Ackley, tools, cases, and loaded rounds. About half the loaded rounds (from the late 1940s) had neck splits, and those that didn't certainly did after I fired them! Sadly, all of the rounds and cases ended up being trash, but they remain the oldest handloads I have used.